Chloramine

chloramine: see hydrazine.

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Chloramine 

any one of a group of chloroderivatives of ammonia (inorganic chloramines) or amines (organic chloramines), whose molecules contain a chlorine atom bonded to nitrogen. (For a discussion of inorganic chloramines, seeNITROGEN CHLORIDE.)

Organic chloramines are liquids or solids, with a pungent odor that irritates the upper respiratory tract. They include the liquids N-chlorodimethylamine, (CH₃)₂NCl, which boils at 46°C, N,N-dichloromethylamine, CH₃NCl₂, which boils at 58°–60°C, and N,N-dichloroethylamine, C₂H₅NCl₂, and N-chlorodiethylamine, (C₂H₅)₂NCl, which boils at 91°C. Hexachloromelamine, whose structural formula is

is a yellow crystalline compound with a melting point of 149°C.

Chloramines decompose in the presence of water, including atmospheric moisture, with the formation of an amine and hypochlorous acid, HOCl. Solutions of chloramines in organic solvents are rather stable. Chloramines are produced by the action of chlorine or hypochlorous acid on amines and amine salts.

The term “chloramine” is often used to denote any N-chloro-derivative of the amides of organic and inorganic acids. Chloramides and dichloramides of aromatic sulfonic acids have found great practical use. Chloramine-B, C₆H₅SO₂NNaCl · 3H₂O (the sodium salt of the N-chloramide of benzenesulfonic acid), and chloramine-T, (CH₃)C₆H₄SO₂NNaCl · 3H₂O (the sodium salt of the N-chloramide of p-toluenesulfonic acid), are colorless crystals with a melting point of 180°–185°C and 175°–180°C, respectively; they are readily soluble in water and ethanol. Dichloramine-B (N,N-dichloro-benzenesulfonamide) and dichloramine-T (N,N-dichloro-p-toluenesulfonamide) are crystals with an odor of chlorine and a melting point of 69°–72°C and 80°–83°C, respectively; they are insoluble in water but soluble in organic solvents, usually dichloroethane.

Chloramines have oxidizing and chlorinating properties and consequently are used in analytical chemistry and in industry, for example, in the textile industry to bleach fabrics; they are also used as decontaminants. In medicine, chloramines, mainly chloramine-B, are used as antiseptics. Chloramine-B, which contains 25–29 percent active chlorine, is also used as a deodorizer and spermatocide. A 0.25–0.5 percent solution of chloramine-B is used to disinfect hands, while a 1–5 percent solution of chloramine-B, chloramine-T, or dichloramine are used to decontaminate utensils and excretions of patients with intestinal and respiratory infections. Chloramines are also used for chlorination of water (Pantocid tablets), treatment of infected wounds, and decontamination of hands and nonmetallic equipment.